Tetrahydrofuran → 3-{[tert-Butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-methyl}1H-indole-6-carboxylic acid methyl ester

HRID 416243Notes

Reaction equation

HRID 416243 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH2:14][NH:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:18][CH:17]=3)=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].C1COCC1.[O:33](C(OC(C)(C)C)=O)[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=O>>[CH3:1][O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([C:9]([CH2:14][N:15]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:33])[C:16]3[CH:17]=[CH:18][C:19]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:20][CH:21]=3)=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 90495Di-tert-butyl dicarbonateHCID 589306603-[(4-Morpholin-4-yl-phenylamino)-methyl]1H-indole-6-carboxylic acid methyl ester

Product 1

HCID 589305773-{[tert-Butoxycarbonyl-(4-morpholin-4-yl-phenyl)-amino]-methyl}1H-indole-6-carboxylic acid methyl esterYield 79%

Procedure

To a solution of 123 (689 mg, 1.89 mmol) in THF (100 ml) Et3N (289 μl, 2.08 mmol) was added dropwise. (BOC)2O was added slowly and the mixture was stirred at room temperature overnight under nitrogen, THF was evaporated off and the residue was partitioned between water and CH2Cl2. Organic layer was separated, dried over MgSO4, evaporated to form another residue which was purified by flash column chromatography (EtOAc/hexane, 7:3) to afford the title compound 124 (692 mg, 79%). 1H-NMR (CDCl3) δ: 8.24 (m, 1H), 8.09 (m, 1H); 7.76 (dd, J=8.2, 1.4 Hz, 1H); 7.55 (d, J=8.8 Hz, 1H); 7.13 (d, J=2.5 Hz, 1H); 6.93 (m, 3H); 4.97 (s, 2H); 3.94 (s, 3H); 3.89 (m, 4H); 3.16 (m, 4H); 1.47 (s, 9H).

Workup

  1. customTHF was evaporated off
  2. customthe residue was partitioned between water and CH2Cl2
  3. customOrganic layer was separated
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customto form another residue which
  7. customwas purified by flash column chromatography (EtOAc/hexane, 7:3)

Sources & evidence

ORD record
ord-b07876775f9e4c948b04f2c0a9adac12
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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