Cesium carbonate → HCID 86731678, compound

HRID 1504787Notes

Reaction equation

HRID 1504787 reaction equation
Br[C:2]1[N:7]=[C:6]([CH2:8][O:9][CH2:10][C:11]([CH3:14])([OH:13])[CH3:12])[CH:5]=[CH:4][CH:3]=1.[C:15](=[O:25])([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH2:16].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:13][C:11]([CH3:14])([CH3:12])[CH2:10][O:9][CH2:8][C:6]1[N:7]=[C:2]([NH:16][C:15](=[O:25])[O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:3]=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 12136Benzyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 583352721-[(6-Bromopyridin-2-yl)methoxy]-2-methylpropan-2-ol

Product 1

HCID 86731678HCID 86731678, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
80 °C

Procedure

To a flask containing 1-[(6-bromopyridin-2-yl)methoxy]-2-methylpropan-2-ol (500 mg, 1.92 mmol), benzyl carbamate (349 mg, 2.31 mmol), Pd2(dba)3 (88 mg, 0.096 mmol), Xantphos (111 mg, 0.192 mmol) and cesium carbonate (939 mg, 2.88 mmol) was added degassed dioxane (15 mL). The flask was evacuated/purged with argon 5 times. The reaction mixture was heated to 80° C. for 18 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (0-50% ethyl acetate/hexanes, linear gradient) to afford benzyl {6-[(2-hydroxy-2-methylpropoxy)methyl]pyridin-2-yl}carbamate. MS ESI calc'd. for C18H23N2O4 [M+H]+ 331. found 331. 1H NMR (500 MHz, CDCl3) δ 7.88 (d, J=8.4 Hz, 1H), 7.69 (t, J=7.9 Hz, 1H), 7.46-7.30 (m, 5H), 7.07 (d, J=7.5 Hz, 1H), 5.22 (s, 2H), 4.57 (s, 2H), 3.39 (s, 2H), 1.24 (s, 6H).

Workup

  1. additionwas added
  2. customdegassed dioxane (15 mL)
  3. customThe flask was evacuated/purged with argon 5 times
  4. temperatureto cool to room temperature
  5. additiondiluted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by chromatography on silica gel (0-50% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-d1a7b381e9604b5cbe5d3acfa1b29260
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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