Water → HCID 90412435, compound

HRID 1522044Notes

Reaction equation

HRID 1522044 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:15](I)=[CH:16][C:9]=23)[CH:5]=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH:36]=2)O1.C(=O)(O)[O-].[Na+].O>CN(C)C=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>[F:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[N:14]([S:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)(=[O:20])=[O:19])[C:15]([C:35]4[CH2:40][CH2:39][N:38]([C:41]([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])=[O:42])[CH2:37][CH:36]=4)=[CH:16][C:9]=23)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 90413104HCID 90413104, compound

Product 1

HCID 90412435HCID 90412435, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 309C (4 g, 7.09 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (2.63 g, 8.51 mmol), Pd(Ph3P)4 (0.410 g, 0.355 mmol), and an aqueous solution (15 mL) of sodium bicarbonate (1.788 g, 21.28 mmol) in dimethylformamide (50 mL) was stirred at 80° C. overnight. The reaction mixture was cooled, treated with water, and extracted with ethyl acetate (three times). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was triturated with a mixture of ethyl acetate and petroleum ether (1:1). The solids were filtered and vacuum oven-dried to give the title compound. MS (ESI+) m/z 535 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate (three times)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was triturated with a mixture of ethyl acetate and petroleum ether (1:1)
  8. filtrationThe solids were filtered
  9. customvacuum oven-dried

Sources & evidence

ORD record
ord-6ffad0c36cd744508357f9bd13a1f21b
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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