Water → HCID 86718025, compound

HRID 1500487Notes

Reaction equation

HRID 1500487 reaction equation
[NH2:1][C:2]1[C:10]2[O:9][CH:8]([CH2:11][OH:12])[CH2:7][C:6]=2[C:5](Br)=[C:4]([CH3:14])[CH:3]=1.[N:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.[C:24]([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>[NH2:1][C:2]1[C:10]2[O:9][CH:8]([CH:11]([OH:12])[CH3:24])[CH2:7][C:6]=2[C:5]([C:18]2[CH:19]=[CH:20][N:15]=[CH:16][CH:17]=2)=[C:4]([CH3:14])[CH:3]=1

Participants

7

Reactant 4

HCID 962Water2×HCID 10796Cesium carbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 86718024HCID 86718024, compound

Product 1

HCID 86718025HCID 86718025, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of (7-amino-4-bromo-5-methyl-2,3-dihydrobenzofuran-2-yl)methanol (7e) (1.7 g, 6.6 mmol), pyridin-4-ylboronic acid (1.6 g, 1.3 mmol), Cs2CO3 (5.3 g, 16 mmol), Pd(PPh3)4 (0.76 g, 0.66 mmol) and water (13 mL) in DMF (60 mL) was stirred at 135° C. under N2 for 1 h. It was cooled to ambient temperature, poured into water (100 mL), extracted with EtOAc (150 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 (7f) as a yellow solid. MS-ESI (m/z): 257 (M+1)+.

Workup

  1. temperatureIt was cooled to ambient temperature
  2. extractionextracted with EtOAc (150 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-a97d18cd1e1f4be8bc60a5d0a0539f06
Source dataset
uspto-grants-2015_12
Patent number
US09206166B2

Reaction notes

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