4-Fluorophenylboronic acid → HCID 21920959, compound

HRID 349587Notes

Reaction equation

HRID 349587 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:13]=1[CH2:14][CH:15]([NH:21][C:22](=[O:30])[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=1)[CH2:16]2.BrC1C=C2C(=CC=1)CC(NC(=O)C1C=CC(F)=CC=1)C2.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>O.C(COC)OC.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]([NH:21][CH:15]2[CH2:16][C:17]3[C:13](=[CH:12][CH:20]=[C:19]([C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH:18]=3)[CH2:14]2)=[O:30])=[CH:24][CH:25]=1

Participants

8

Reactant 4

HCID 2856454-Fluorophenylboronic acidHCID 17749109Barium hydroxide, octahydrateHCID 21921016HCID 21921016, compoundHCID 21921107HCID 21921107, compound

Product 1

HCID 21920959HCID 21920959, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

251 mg (1.8 mmol) 4-fluorobenzene boronic acid, 500 mg (1.5 mmol) of a mixture of N-(4-bromo-indan-2-yl)-4-fluoro-benzamide (relative amount 20%) and N-(5-bromo-indan-2-YL)-4-fluoro-benzamide (relative amount 80%), 708 mg (2.24 mmol) barium hydroxide octahydrate and 50 mg tetrakis(triphenylphosphine)-palladium were suspended in 10 ml of water and 10 ml of dimethoxyethane, under an argon atmosphere, and stirred over 2 h at 80° C. The mixture was poured onto ice water, the formed precipitate was filtered off and crystallized from ethyl acetate/hexane. 170 mg (27%) 4-fluoro-N-[5-(4-fluorophenyl)-indan-2-yl]-benzamide, mp.: 193° C., were obtained.

Workup

  1. additionThe mixture was poured onto ice water
  2. filtrationthe formed precipitate was filtered off
  3. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-47aff3e194c04456b5dbd37b480be688
Source dataset
uspto-grants-2007_02
Patent number
US07179839B2

Reaction notes

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