4-Bromoaniline → HCID 178462391, compound

HRID 480955Notes

Reaction equation

HRID 480955 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.C[Al](C)C.[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[C@@:21]([OH:47])([CH2:41][N:42]1[CH:46]=[N:45][CH:44]=[N:43]1)[C@H:22]([S:24][C@@H:25]1[CH2:30][O:29][C@@H:28]([C:31]2[CH:40]=[CH:39][C:34]([C:35](OC)=[O:36])=[CH:33][CH:32]=2)[O:27][CH2:26]1)[CH3:23]>>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:35](=[O:36])[C:34]2[CH:39]=[CH:40][C:31]([C@H:28]3[O:27][CH2:26][C@H:25]([S:24][C@H:22]([CH3:23])[C@:21]([C:15]4[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=4[F:13])([OH:47])[CH2:41][N:42]4[CH:46]=[N:45][CH:44]=[N:43]4)[CH2:30][O:29]3)=[CH:32][CH:33]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 78074-BromoanilineHCID 16682925TrimethylaluminumHCID 178497884HCID 178497884, compound

Product 1

HCID 178462391HCID 178462391, compoundYield 95%

Procedure

In the same manner as that described in Example 3(4), a reaction was carried out using commercially available 4-bromoaniline (205 mg, 1.2 mmol), trimethylaluminium (1.1 ml, 1.07M n-hexane solution, 1.2 mmol) and methyl 4-[trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]benzoate (150 mg, 0.30 mmol), obtained in Example 12(1), and the reaction mixture was treated using a similar procedure to that described in Example 3(4) to afford the title compound (182 mg, yield 95%) as a white solid which was recrystallized from ethyl acetate to give white powdery crystals.

Workup

  1. customobtained in Example 12(1)
  2. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-e4338c8b223448c698358c709d18303d
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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