N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide → N-(2-t-butoxycarbonylaminophenyl)-4-[2-(2-pyrrolidin-1-ylethoxy)pyrimidin-5-yl]benzamide

HRID 888033Notes

Reaction equation

HRID 888033 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20](B2OC(C)(C)C(C)(C)O2)=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:34]1[CH:35]=[N:36][C:37]([O:40][CH2:41][CH2:42][N:43]2[CH2:47][CH2:46][CH2:45][CH2:44]2)=[N:38][CH:39]=1>>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16](=[O:32])[C:17]1[CH:22]=[CH:21][C:20]([C:34]2[CH:39]=[N:38][C:37]([O:40][CH2:41][CH2:42][N:43]3[CH2:47][CH2:46][CH2:45][CH2:44]3)=[N:36][CH:35]=2)=[CH:19][CH:18]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

3

Reactant 2

HCID 59830883N-(2-t-Butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamideHCID 63867546HCID 63867546, compound

Product 1

HCID 68406999N-(2-t-butoxycarbonylaminophenyl)-4-[2-(2-pyrrolidin-1-ylethoxy)pyrimidin-5-yl]benzamideYield 28.2%

Procedure

Using an analogous procedure to that described in Method 44, N-(2-t-butoxycarbonylaminophenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (Method 13, 219 mg, 0.5 mmol) was reacted with 5-bromo-2-(2-pyrrolidin-1-ylethoxy)pyrimidine (Method 64, 136 mg, 0.5 mmol) to give the title compound (71 mg; 28%). Mass Spectrum: M+H+ 504.

Sources & evidence

ORD record
ord-1ff8e7c7f9c64402a5e9f4d27cdda6b5
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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