Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate → HCID 67119257, compound

HRID 2076644Notes

Reaction equation

HRID 2076644 reaction equation
Br[CH2:2][C:3]1[C:8]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:7]([O:16]C(OC(C)(C)C)=O)[C:6]([C:24]([F:27])([F:26])[F:25])=[CH:5][CH:4]=1.[OH:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]2[N:40]=[CH:39][C:38]([CH2:41][C:42]([O:44][CH2:45][CH:46]=[CH2:47])=[O:43])=[CH:37][N:36]=2)=[CH:31][CH:30]=1>>[CH2:45]([O:44][C:42]([CH2:41][C:38]1[CH:37]=[N:36][C:35]([C:32]2[CH:31]=[CH:30][C:29]([O:28][CH2:2][C:3]3[C:8]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])=[C:7]([OH:16])[C:6]([C:24]([F:26])([F:25])[F:27])=[CH:5][CH:4]=3)=[CH:34][CH:33]=2)=[N:40][CH:39]=1)=[O:43])[CH:46]=[CH2:47]

Participants

3

Reactant 2

HCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoateHCID 136355280HCID 136355280, compound

Product 1

HCID 67119257HCID 67119257, compoundYield 28%

Procedure

According to a method similar to Example (2-3) and Example (33-5), from tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (412 mg, 0.92 mmol) obtained in Example (28-5) and allyl [2-(4-hydroxyphenyl)-5-pyrimidinyl]acetate (250 mg, 0.92 mmol), tert-butyl 6-{[4-(5-{[(allyloxy)carbonyl]methyl}-2-pyrimidinyl)phenoxy]methyl}-2-hydroxy-3-(trifluoromethyl)benzoate was obtained (140 mg, two-step total yield: 28%).

Sources & evidence

ORD record
ord-ab9cb3b0bc7e435ca9e1d5481654e997
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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