2-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → Methyl 2-fluoro-4-{5-[2'-methoxy-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate

HRID 219951Notes

Reaction equation

HRID 219951 reaction equation
CC1C=C(C(O)=O)C=CC=1C1C=CC=CC=1C(F)(F)F.Br[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[O:32][N:31]=[C:30]([C:33]3[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[C:35]([F:43])[CH:34]=3)[N:29]=2)=[CH:24][C:23]=1[CH2:44][O:45][CH3:46].[CH3:47][O:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1B1OC(C)(C)C(C)(C)O1>>[F:43][C:35]1[CH:34]=[C:33]([C:30]2[N:29]=[C:28]([C:25]3[CH:26]=[CH:27][C:22]([C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=4[O:48][CH3:47])=[C:23]([CH2:44][O:45][CH3:46])[CH:24]=3)[O:32][N:31]=2)[CH:42]=[CH:41][C:36]=1[C:37]([O:39][CH3:40])=[O:38]

Participants

4

Reactant 3

HCID 114020492-(2-Methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 219478123-Methyl-4-[2-(trifluoromethyl)phenyl]benzoic acidHCID 67528348Methyl 4-{5-[4-bromo-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

Product 1

HCID 67528482Methyl 2-fluoro-4-{5-[2'-methoxy-2-(methoxymethyl)biphenyl-4-yl]-1,2,4-oxadiazol-3-yl}benzoate

Procedure

Title compound was prepared following procedure and work up described for Intermediate 5 step 2 but starting from methyl 4-{5-[4-bromo-3-(methoxymethyl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate obtained from step 1 (50 mg, 0.12 mmol) and 2-(2-methoxy-phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30.5 mg, 0.13 mmol) (130° C. for 10 min under microwave irradiation). Purification by flash chromatography (cHex:EtOAc, from 100:0 to 20:80) gave the title compound as a yellow powder. LC/MS (Method B): 449.2 (M+H)+.

Workup

  1. customTitle compound was prepared
  2. customPurification by flash chromatography (cHex:EtOAc, from 100:0 to 20:80)

Sources & evidence

ORD record
ord-d5834a286fdf49d09123732e338233a8
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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