1-Bromo-3,5-difluorobenzene → HCID 178505933, compound

HRID 2415614Notes

Reaction equation

HRID 2415614 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:18][CH2:17][C@@H:16]([NH2:19])[CH2:15][CH2:14]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.Br[C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:14][CH2:15][C@@H:16]([NH:19][C:21]4[CH:26]=[C:25]([F:27])[CH:24]=[C:23]([F:28])[CH:22]=4)[CH2:17][CH2:18]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1363131-Bromo-3,5-difluorobenzeneHCID 634876Binap, (A+-)-HCID 178511631HCID 178511631, compound

Product 1

HCID 178505933HCID 178505933, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Procedure

A mixture of example 23A (30 mg, 0.11 mmol), 1-bromo-3,5-difluorobenzene (25 mg, 0.132 mmol), Pd2(dba)3 (1 mg, 0.001 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphtyl (1.6 mg, 002 mmol) and sodium-tert-btoxide (14 mg, 0.132 mmol) was heated for 15 hours in ethyleneglycoldimethylether, concentrated and the residue was purified with high throughput HPLC system to provide the desired compound as its bis trifluoroacetic acid salt. MS (ESI(+)Q1MS m/z 388 (M+H)+); 1H NMR (300 MHz, DMSO-D6) δ ppm 8.91 (d, 1 H), 8.71 (d, 1 H), 8.55 (d, 1 H), 7.92 (d, 1 H), 7.80 (dd, 1 H), 7.01 (d, 1 H), 6.25 (m, 4 H), 3.86-4.10 (br.s, 1 H), 3.54 (br.s, 1 H), 3.54 (m, 8 H).

Workup

  1. concentrationconcentrated
  2. customthe residue was purified with high throughput HPLC system

Sources & evidence

ORD record
ord-bfe75ad0c6e441a7bc54132ed819aa50
Source dataset
uspto-grants-2004_11
Patent number
US06818772B2

Reaction notes

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