Potassium Phosphate, Tribasic → methyl 2-(8-(4-(dimethylcarbamoyl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)-2-methylpropanoate

HRID 1663411Notes

Reaction equation

HRID 1663411 reaction equation
[CH3:1][C:2]([CH:8]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[O:15][C:14]2[C:9]1=[CH:10][CH:11]=[C:12](B1OC(C)(C)C(C)(C)O1)[CH:13]=2)([CH3:7])[C:3]([O:5][CH3:6])=[O:4].Br[C:32]1[CH:42]=[CH:41][C:35]([C:36]([N:38]([CH3:40])[CH3:39])=[O:37])=[CH:34][CH:33]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.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>[CH3:39][N:38]([CH3:40])[C:36]([C:35]1[CH:41]=[CH:42][C:32]([C:12]2[CH:13]=[C:14]3[C:9]([CH:8]([C:2]([CH3:1])([CH3:7])[C:3]([O:5][CH3:6])=[O:4])[C:21]4[C:16]([O:15]3)=[N:17][CH:18]=[CH:19][CH:20]=4)=[CH:10][CH:11]=2)=[CH:33][CH:34]=1)=[O:37]

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 1403894-bromo-N,N-dimethylbenzamideHCID 67436382methyl 2-methyl-2-(8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-chromeno[2,3-b]pyridin-5-yl)propanoate

Product 1

HCID 67435392methyl 2-(8-(4-(dimethylcarbamoyl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)-2-methylpropanoateYield 73%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product from Step 5 (65 mg, 0.159 mmol), 4-bromo-N,N-dimethylbenzamide (72.4 mg, 0.318 mmol), 2.0 M aqueous potassium phosphate (0.397 mL, 0.794 mmol) and Pd(Ph3P)4 (27.5 mg, 0.024 mmol) in DMF (3 mL) was purged with N2, heated to 100° C. for 15 h, and cooled to room temperature. After addition of ethyl acetate (80 mL), the mixture was washed with water (10 mL), brine (10 mL), dried (MgSO4) and concentrated. The residue was purified by flash column chromatography (silica, 30-100% ethyl acetate in hexanes) to provide methyl 2-(8-(4-(dimethylcarbamoyl)phenyl)-5H-chromeno[2,3-b]pyridin-5-yl)-2-methylpropanoate (50 mg, 73%). MS (ES+) m/z: 431 (M+H).

Workup

  1. customwas purged with N2
  2. temperaturecooled to room temperature
  3. additionAfter addition of ethyl acetate (80 mL)
  4. washthe mixture was washed with water (10 mL), brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (silica, 30-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6ab1e05c71e84483888a3f5f467c4d4b
Source dataset
uspto-grants-2011_10
Patent number
US08034940B2

Reaction notes

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