{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester → (1-[4-(5-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl ester

HRID 1037160Notes

Reaction equation

HRID 1037160 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27](=[O:28])[C:26]4[C:21](=[CH:22][CH:23]=[C:24](F)[CH:25]=4)[O:20][C:19]=3C3C=CC=CC=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[F:37][C:38]1[CH:47]=[CH:46][CH:45]=[C:44]2[C:39]=1C(=O)C(I)=C(C1C=CC=CC=1)O2>>[C:1]([O:5][C:6](=[O:36])[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:19](=[O:20])[C:47]4[C:46](=[CH:45][CH:44]=[CH:39][C:38]=4[F:37])[O:28][C:27]=3[C:26]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:14][CH:13]=2)[CH2:9][CH2:10][CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 67067635{1-[4-(6-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl esterHCID 670676545-Fluoro-3-iodo-2-phenyl-chromen-4-one

Product 1

HCID 67067716(1-[4-(5-Fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl)-carbamic acid tert-butyl esterYield 26%

Procedure

Following the procedure used to prepare {1-[4-(6-fluoro-4-oxo-2-phenyl-4H-chromen-3-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester, 5-fluoro-3-iodo-2-phenyl-chromen-4-one (55 mg, 0.15 mmol) was reacted to give the title compound (19 mg, 26%). 1H NMR (400 MHz, CDCl3): δ 7.65-7.57 (m, 1H), 7.41-7.29 (m, 6H), 7.28-7.22 (m, 2H), 7.21-7.16 (m, 2H), 7.09-7.03 (m, 1H), 5.03 (s, 1H), 2.61-2.29 (m, 4H), 2.21-2.00 (m, 1H), 1.88-1.74 (m, 1H), 1.48-1.18 (m, 9H).

Workup

  1. customwas reacted

Sources & evidence

ORD record
ord-fedba0b5de0f4a8f97b25c98b984d243
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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