Water → HCID 178505498, compound

HRID 1666114Notes

Reaction equation

HRID 1666114 reaction equation
Br[C:2]1[C:11]2[CH2:10][O:9][C:8]([NH:12][C@H:13]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][CH2:14]3)=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC>[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:2]2[C:11]3[CH2:10][O:9][C:8]([NH:12][C@H:13]4[C:21]5[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=5)[CH2:15][CH2:14]4)=[N:7][C:6]=3[CH:5]=[CH:4][CH:3]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 178419341HCID 178419341, compound

Product 1

HCID 178505498HCID 178505498, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A stirred mixture of (5-bromo-4H-benzo[d][1,3]oxazin-2-yl) -(R)-indan-1-yl-amine (Example 10) (171.6 mg, 0.5 mmol), 4-fluorophenyl-boronic acid (84 mg, 0.6 mmol), 1M sodium carbonate solution (1.25 ml, 1.25 mmol), tetarkis(triphenylphosphine)palladium (17.3 mg, 0.015 mmol) in 1,2-dimethoxy-ethane (2.5 ml) was heated at 80° C. for 17 h. The reaction mixture was poured into water (20 ml), extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with water (20 ml) and brine (20 ml), dried (MgSO4) and evaporated. Further purification by flash chromatography (ethyl acetate/heptane) on silica gel yielded the title compound as white foam (164 mg, 92%). MS (ISP) m/e=359.1 [(M+H)+].

Workup

  1. extractionextracted with ethyl acetate (2×30 ml)
  2. washThe combined organic layers were washed with water (20 ml) and brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customFurther purification by flash chromatography (ethyl acetate/heptane) on silica gel

Sources & evidence

ORD record
ord-c7576dc201364157bcebf2e6d41ad50b
Source dataset
uspto-grants-2011_10
Patent number
US08044047B2

Reaction notes

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