1-(t-Butoxycarbonyl)-3-(chloromethyl)-6-nitroindoline → 2-[3-(chloromethyl)-6-nitro-indoline-1-carbonyl]-N-[2-hydroxy-1-(hydroxymethyl)ethyl]-1H-indole-6-carboxamide

HRID 1603047Notes

Reaction equation

HRID 1603047 reaction equation
C(O[C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=2)[CH:10]([CH2:20][Cl:21])[CH2:9]1)=[O:7])(C)(C)C.C([C:25]1[NH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][CH:30]=[C:29]([C:34]([NH:36][CH:37]([CH2:40][OH:41])[CH2:38][OH:39])=[O:35])[CH:28]=2)(O)=O>CCOC(C)=O>[Cl:21][CH2:20][CH:10]1[C:11]2[C:16](=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[N:8]([C:6]([C:25]2[NH:26][C:27]3[C:32]([CH:33]=2)=[CH:31][CH:30]=[C:29]([C:34]([NH:36][CH:37]([CH2:38][OH:39])[CH2:40][OH:41])=[O:35])[CH:28]=3)=[O:7])[CH2:9]1

Participants

4

Reactant 2

HCID 108289531-(t-Butoxycarbonyl)-3-(chloromethyl)-6-nitroindolineHCID 196087812-carboxy-N-(1,3-dihydroxy-2-propyl)indole-6-carboxamide

Product 1

HCID 3905052-[3-(chloromethyl)-6-nitro-indoline-1-carbonyl]-N-[2-hydroxy-1-(hydroxymethyl)ethyl]-1H-indole-6-carboxamideYield 29%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-(t-Butoxycarbonyl)-3-(chloromethyl)-6-nitroindoline was coupled with 2-carboxy-N-(1,3-dihydroxy-2-propyl)indole-6-carboxamide by the method described above, the EtOAc layer dried (Na2SO4), evaporated, and the residue recrystallised from EtOH to give 2-[[3-(chloromethyl)-6-nitroindolin-1-yl]carbonyl]-N-(1,3-dihydroxy-2-propyl)indole-6-carboxamide as a cream powder (29%), mp 230-231° C. (dec.). 1H NMR [(CD3)2SO] δ12.13 (s, 1H, indole NH), 8.98 (d, J=2.1 Hz, 1H, H-7), 8.05 (dd, J=8.3, 2.2 Hz, 1H, H-5), 8.04 (s, 1H, H-3' or H-7'), 7.95 (d, J=8.0 Hz, 1H, amide NH), 7.76 (d, J=8.5 Hz, 1H, H-4'), 7.75 (d, J=8.3 Hz, 1H, H-4), 7.61 (dd, J=8.5, 1.4 Hz, 1H, H-5'), 7.29 (d, J=1.6 Hz, 1H, H-3' or H-7'), 4.87 (t, J=10.1 Hz, 1H, H-2), 4.70 (t, J=5.7 Hz, 2H, OH), 4.51 (dd, J=10.7, 5.1 Hz, 1H, H-2), 4.19-4.06 (m, 3H, H-3 and CH2Cl), 4.04-3.97 (m, 1H, CONHCH), 3.55 (t, J=5.7 Hz, 4H, CH2OH); 13C NMR δ166.8 (CONH), 160.4 (CON), 147.6, 144.6, 139.9, 135.7, 131.8, 131.0, 128.9 (C-6,8,9,2',6',8',9'), 125.5, 121.4, 119.4, 119.1, 112.2, 111.2, 106.1 (C-4,5,7,3',4',5',7'), 60.4 (CH2OH), 54.0 (C-2), 53.8 (CONHCH), 47.0 (CH2Cl), 42.0 (C-3). Anal. (C22H21,ClN4O6).

Workup

  1. dry with materialdried (Na2SO4)
  2. customevaporated
  3. customthe residue recrystallised from EtOH

Sources & evidence

ORD record
ord-7973dff5431243f7999af24fc27a4a9e
Source dataset
uspto-grants-1999_11
Patent number
US05985909

Reaction notes

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