3-甲基苯胺 → tert-butyl (1S,2R)-2-(4-cyano-3-(m-tolylamino)phenylamino)cyclohexylcarbamate

HRID 84792

反应方程式

HRID 84792 反应方程式
Br[C:2]1[CH:3]=[C:4]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[CH:27]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:8]([C:7]1[CH:6]=[CH:5][C:4]([NH:10][C@@H:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@@H:12]2[NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:3][C:2]=1[NH:25][C:26]1[CH:27]=[C:28]([CH3:32])[CH:29]=[CH:30][CH:31]=1)#[N:9]

参与物

7

反应物 4

HCID 79343-甲基苯胺HCID 10796碳酸氢铯HCID 6348761,1'-联萘-2,2'-双二苯膦 (BINAP)HCID 69283621tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate

产物 1

HCID 69284029tert-butyl (1S,2R)-2-(4-cyano-3-(m-tolylamino)phenylamino)cyclohexylcarbamate

试剂、催化剂与溶剂 2

HCID 167845palladium acetate催化剂HCID 1140甲苯溶剂

实验过程

A mixture of tert-butyl (1S,2R)-2-(3-bromo-4-cyanophenylamino)cyclohexylcarbamate (98 mg, 0.25 mmol), m-toluidine (54 uL, 0.50 mmol), BINAP (31 mg, 0.050 mmol), Pd(OAc)2 (12 mg, 0.053 mmol) and Cs2CO3 (160 mg, 0.49 mmol) in toluene (3 mL) was degassed with Ar, then was stirred at 100 C for 3 h. EtOAc and water were added. The organic phase was separated, washed with 1N HCl, then with brine, dried over Na2SO4, concentrated in vacuo to give tert-butyl (1S,2R)-2-(4-cyano-3-(m-tolylamino)phenylamino)cyclohexylcarbamate as a residue.

后处理

  1. customwas degassed with Ar
  2. additionEtOAc and water were added
  3. customThe organic phase was separated
  4. washwashed with 1N HCl
  5. dry with materialwith brine, dried over Na2SO4
  6. concentrationconcentrated in vacuo

来源与证据

ORD记录
ord-47449be5950b4000a5aa0d6e3bbc9d3d
来源数据集
uspto-grants-2014_09
专利号
US08846928B2

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