Methanol → HCID 118340992, compound

HRID 629851Notes

Reaction equation

HRID 629851 reaction equation
C([O-])([O-])=O.[Na+].[Na+].CO.[CH:9]1([NH:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2B2OC(C)(C)C(C)(C)O2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.Br[C:37]1[N:42]=[C:41]([CH:43]=[O:44])[CH:40]=[CH:39][CH:38]=1>O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[CH:9]1([NH:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2[C:37]2[N:42]=[C:41]([CH:43]=[O:44])[CH:40]=[CH:39][CH:38]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

8

Reactant 4

HCID 887MethanolHCID 10340Sodium CarbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 131735385HCID 131735385, compound

Product 1

HCID 118340992HCID 118340992, compound

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 21.2 g (74.1 mmol) of Na2CO3×10H2O in 660 ml of water and 190 ml of methanol was purged with argon for 30 min. The obtained solution was added to a mixture of 29.9 g (80.0 mmol) of cyclohexyl{[1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-naphthyl]methyl}amine, 14.0 g (80.0 mmol) of 6-bromopyridine-2-carbaldehyde, 4.62 g (4.00 mmol) of Pd(PPh3)4, and 780 ml of toluene in argon atmosphere. This mixture was refluxed for 10 h using a mechanical stirrer, then cooled to room temperature. The organic layer was separated, dried over Na2SO4, evaporated to 300 ml in volume, and then extracted with 3×300 ml of 2M HCl. The combined aqueous layer was alkalified to pH 10 by the saturated aqueous K2CO3, and then extracted with 3×200 ml of dichloromethane. The combined organic extract was dried over Na2SO4 and evaporated to dryness. Yield 23.1 g (84%) of a brown oil. Anal. Calc for C23H24N2O: C 80.20; H 7.02; N 8.13. Found: C 80.78; H 7.11; N 8.01.1H NMR (CDCl3): δ 10.08 (s, 1H, CHO), 7.96-8.03 (m, 2H, 3-H, 4-H in Py), 7.83-7.89 (m, 2H, 8,5-H in Py), 7.59-7.64 (m, 2H, 5-H in Py and 4-H in naphthyl), 7.39-7.43 (m, 1H, 6-H in naphthyl), 7.30-7.34 (m, 1H, 7-H in naphthyl), 7.20-7.23 (m, 1H, 3-H in naphthyl), 3.56 (m, 2H, CH2), 2.21 (m, 1H, 1-H in Cy), 1.57-1.66 (m, 4H, Cy), 1.02-1.11 (m, 4H, Cy), 0.88-0.96 (m, 2H, Cy).

Workup

  1. temperatureThis mixture was refluxed for 10 h
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. customevaporated to 300 ml in volume
  5. extractionextracted with 3×300 ml of 2M HCl
  6. extractionextracted with 3×200 ml of dichloromethane
  7. extractionThe combined organic extract
  8. dry with materialwas dried over Na2SO4
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-a6a19c1e0f2f41bfa93d01f8037e1101
Source dataset
uspto-grants-2016_04
Patent number
US09315526B2

Reaction notes

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