Water → HCID 86718029, compound

HRID 1500491Notes

Reaction equation

HRID 1500491 reaction equation
Br[C:2]1[C:7]2[CH2:8][CH:9]([CH2:11][O:12][CH3:13])[O:10][C:6]=2[C:5]([NH2:14])=[CH:4][C:3]=1[CH3:15].[N:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>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>[CH3:13][O:12][CH2:11][CH:9]1[CH2:8][C:7]2[C:2]([C:19]3[CH:20]=[CH:21][N:16]=[CH:17][CH:18]=3)=[C:3]([CH3:15])[CH:4]=[C:5]([NH2:14])[C:6]=2[O:10]1

Participants

7

Reactant 4

HCID 962Water2×HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86718030HCID 86718030, compound

Product 1

HCID 86718029HCID 86718029, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 4-bromo-2-(methoxymethyl)-5-methyl-2,3-dihydrobenzofuran-7-amine (8c) (0.85 g, 3.1 mmol), pyridin-4-ylboronic acid (0.76 g, 6.2 mmol), Cs2CO3 (2.5 g, 7.8 mmol), Pd(PPh3)4 (0.18 g, 0.16 mmol) and water (6 mL) in DMF (20 mL) was stirred at 135° C. under N2 for 1 h. It was cooled to ambient temperature, poured into water (50 mL), extracted with EtOAc (60 mL), washed with water, brine, dried and concentrated. The residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1 to 5:1 to 1:1) to give the title compound (8d) as a yellow oil. MS-ESI (m/z): 271 (M+1)+.

Workup

  1. temperatureIt was cooled to ambient temperature
  2. extractionextracted with EtOAc (60 mL)
  3. washwashed with water, brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel eluting with hexanes/EtOAc (20:1 to 5:1 to 1:1)

Sources & evidence

ORD record
ord-35aebdfb622a4a60ac57c4fdc531b0e1
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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