1-(tert-Butoxycarbonyl)-2-pyrroleboronic Acid → 2-{5-[(3,5-Bis-trifluoromethyl-benzoyl)-methyl-amino]-4-o-tolyl-pyridin-2-yl}-pyrrole-1-carboxylic acid tert-butyl ester

HRID 878111Notes

Reaction equation

HRID 878111 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:25])[C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[CH:3]=1.[C:33]([O:37][C:38]([N:40]1[CH:44]=[CH:43][CH:42]=[C:41]1B(O)O)=[O:39])([CH3:36])([CH3:35])[CH3:34]>CCCCCCC.CCOC(C)=O>[C:33]([O:37][C:38]([N:40]1[CH:44]=[CH:43][CH:42]=[C:41]1[C:2]1[CH:3]=[C:4]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH3:32])[C:5]([N:8]([C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:18])([F:17])[F:19])[CH:13]=[C:12]([C:20]([F:22])([F:23])[F:21])[CH:11]=2)[CH3:25])=[CH:6][N:7]=1)=[O:39])([CH3:36])([CH3:34])[CH3:35]

Participants

4

Reactant 2

HCID 27343211-(tert-Butoxycarbonyl)-2-pyrroleboronic AcidHCID 60197100N-(6-Chloro-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

Product 1

HCID 866707352-{5-[(3,5-Bis-trifluoromethyl-benzoyl)-methyl-amino]-4-o-tolyl-pyridin-2-yl}-pyrrole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 72, from N-(6-chloro-4-o-tolyl-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (example 12) and 1-(tert-butoxycarbonyl)pyrrole-2-boronic acid (CAS RN 135884-31-0) and using a gradient of n-heptane:EtOAc (100:0 to 50:50) for the chromatographic purification. Light yellow oil (18%). MS (ESI): m/z=604.202 [M+H]+.

Workup

  1. customfor the chromatographic purification

Sources & evidence

ORD record
ord-c9472cdd3c1142208b533be441899643
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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