Methyl 3'-(bromomethyl)-4-chlorobiphenyl-3-carboxylate → 4-Chloro-3'-((2-cyclohexyl-3-oxo-2,3-dihydrobenzo[d]isoxazol-6-yloxy)methyl)biphenyl-3-carboxylic acid

HRID 404975Notes

Reaction equation

HRID 404975 reaction equation
[CH:1]1([N:7]2[C:11](=[O:12])[C:10]3[CH:13]=[CH:14][C:15]([OH:17])=[CH:16][C:9]=3[O:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:19][C:20]1[CH:21]=[C:22]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([O:35]C)=[O:34])[CH:27]=2)[CH:23]=[CH:24][CH:25]=1>>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([C:22]2[CH:23]=[CH:24][CH:25]=[C:20]([CH2:19][O:17][C:15]3[CH:14]=[CH:13][C:10]4[C:11](=[O:12])[N:7]([CH:1]5[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]5)[O:8][C:9]=4[CH:16]=3)[CH:21]=2)=[CH:27][C:28]=1[C:33]([OH:35])=[O:34]

Participants

3

Reactant 2

HCID 50994825Methyl 3'-(bromomethyl)-4-chlorobiphenyl-3-carboxylateHCID 667996302-Cyclohexyl-6-hydroxybenzo[d]isoxazol-3(2H)-one

Product 1

HCID 533908344-Chloro-3'-((2-cyclohexyl-3-oxo-2,3-dihydrobenzo[d]isoxazol-6-yloxy)methyl)biphenyl-3-carboxylic acidYield 31%

Procedure

2-Cyclohexyl-6-hydroxybenzo[d]isoxazol-3(2H)-one (0.100 g, 0.43 mmol) and methyl 3′-(bromomethyl)-4-chlorobiphenyl-3-carboxylate (0.174 g, 0.51 mmol) were processed according to the general procedure for Example 23 to provide 4-chloro-3′-((2-cyclohexyl-3-oxo-2,3-dihydrobenzo[d]isoxazol-6-yloxy)methyl)biphenyl-3-carboxylic acid in 31% yield over 2 steps (0.034 g) as a colorless solid. 1H NMR (DMSO-d6): δ 8.01 (s, 1H), 7.81 (d, 1H, J=8.6 Hz), 7.79 (d, 1H, J=8.5 Hz), 7.63-7.58 (m, 3H), 7.49-7.48 (m, 2H), 7.15 (s, 1H), 6.95 (d, 1H, J=8.6 Hz), 5.23 (s, 2H), 4.19-4.18 (m, 1H), 1.76-1.69 (m, 7H), 1.66-1.64 (m, 3H). HRMS (ESI)Calcd for C267H24ClNO5 [M+H]+: 478.1416. Found: 478.1418.

Sources & evidence

ORD record
ord-8ffe069a8393497fa46e9b253d98c8cb
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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