1-Bromo-4-fluorobenzene → HCID 58975060, compound

HRID 737040Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][CH:3]=1.[NH:9]1[CH2:12][CH:11]([NH:13][C:14](=[O:39])[C:15]2[CH:20]=[CH:19][C:18]([S:21]([N:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:25]3)(=[O:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C(Cl)Cl.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]>[F:8][C:5]1[CH:6]=[CH:7][C:2]([N:9]2[CH2:12][CH:11]([NH:13][C:14](=[O:39])[C:15]3[CH:20]=[CH:19][C:18]([S:21]([N:24]4[C:32]5[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=5)[C:26]([C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)=[CH:25]4)(=[O:22])=[O:23])=[CH:17][CH:16]=3)[CH2:10]2)=[CH:3][CH:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Add 1-bromo-4-fluorobenzene (110 μL, 180 mg, 1.0 mmol, 2.0 equiv) to a mixture of N-azetidin-3-yl-4-(3-phenyl-indole-1-sulfonyl)-benzamide (216 mg, 0.501 mmol, 1 equiv), tris(dibenzylideneacetone)dipalladium(0) (12 mg, 0.012 mmol, 0.025 equiv), 2-(di-tert-butylphosphino)biphenyl (8 mg, 0.03 mmol, 0.05 equiv), and sodium tert-butoxide (58 mg, 0.60 mmol, 1.2 equiv) in anhydr toluene (2 mL). Heat the reaction mixture at 100° C. for 14 h. After cooling, dilute the reaction mixture with CH2Cl2 and transfer through a 0.45-μm filter disc to a column of silica gel (80 mm×20 mm dia.) and elute (10-35% EtOAc/hex) to yield 63 mg (24%) of N-[1-(4-fluoro-phenyl)-azetidin-3-yl]-4-(3-phenyl-indole-1-sulfonyl)-benzamide as a white solid.

Workup

temperatureAfter cooling
filtrationfilter disc to a column of silica gel (80 mm×20 mm dia.)
washelute (10-35% EtOAc/hex)

Sources & evidence

ORD record: ord-2c200477be924825afa560c5dc7e4199
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595339B2

Reaction notes

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