5-(4-Methylbenzyl)-benzofuran-2-ylboronic acid → Methyl 1-(3-fluoro-4-(5-(4-methylbenzyl)benzofuran-2-yl)benzyl)azetidine-3-carboxylate

HRID 2075171Notes

Reaction equation

HRID 2075171 reaction equation
[CH3:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][C:7]2[CH:8]=[CH:9][C:10]3[O:14][C:13](B(O)O)=[CH:12][C:11]=3[CH:18]=2)=[CH:4][CH:3]=1.Br[C:22]1[CH:36]=[CH:35][C:25]([CH2:26][N:27]2[CH2:30][CH:29]([C:31]([O:33][CH3:34])=[O:32])[CH2:28]2)=[CH:24][C:23]=1[F:37]>>[F:37][C:23]1[CH:24]=[C:25]([CH:35]=[CH:36][C:22]=1[C:13]1[O:14][C:10]2[CH:9]=[CH:8][C:7]([CH2:6][C:5]3[CH:19]=[CH:20][C:2]([CH3:1])=[CH:3][CH:4]=3)=[CH:18][C:11]=2[CH:12]=1)[CH2:26][N:27]1[CH2:28][CH:29]([C:31]([O:33][CH3:34])=[O:32])[CH2:30]1

Participants

3

Reactant 2

HCID 584152975-(4-Methylbenzyl)-benzofuran-2-ylboronic acidHCID 59651823Methyl 1-(4-bromo-3-fluorobenzyl)azetidine-3-carboxylate

Product 1

HCID 58415298Methyl 1-(3-fluoro-4-(5-(4-methylbenzyl)benzofuran-2-yl)benzyl)azetidine-3-carboxylate

Procedure

In a similar manner as described in general procedure D, 5-(4-methylbenzyl)-benzofuran-2-ylboronic acid (150 mg, 0.56 mmol) was reacted with methyl 1-(4-bromo-3-fluorobenzyl)azetidine-3-carboxylate (155 mg, 0.51 mmol) to give methyl 1-(3-fluoro-4-(5-(4-methylbenzyl)benzofuran-2-yl)benzyl)azetidine-3-carboxylate as white solid: MS (ESI) m/z: Calculated: 443.51; Observed: 444.0 (M++1).

Sources & evidence

ORD record
ord-f450265027c3485c92f5098649d6d355
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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