Diisopropylethylamine → tert-butyl-2-bromo-1-(2-{(2-bromo-5-chlorobenzyl)[2-(dimethylamino)ethyl]amino}-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1714007Notes

Reaction equation

HRID 1714007 reaction equation
[Br:1][C:2]1[N:3]([CH2:24][C:25](O)=[O:26])[C:4]2[C:9]([C:10]=1[CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[CH:8][CH:7]=[C:6]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=2.[Br:28][C:29]1[CH:41]=[CH:40][C:39]([Cl:42])=[CH:38][C:30]=1[CH2:31][NH:32][CH2:33][CH2:34][N:35]([CH3:37])[CH3:36].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:20]([O:19][C:17]([C:6]1[CH:5]=[C:4]2[C:9]([C:10]([CH:11]3[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]3)=[C:2]([Br:1])[N:3]2[CH2:24][C:25]([N:32]([CH2:31][C:30]2[CH:38]=[C:39]([Cl:42])[CH:40]=[CH:41][C:29]=2[Br:28])[CH2:33][CH2:34][N:35]([CH3:37])[CH3:36])=[O:26])=[CH:8][CH:7]=1)=[O:18])([CH3:21])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66160827N'-(2-bromo-5-chlorobenzyl)-N,N-dimethylethane-1,2-diamineHCID 68509336[2-bromo-6-(tert-butoxycarbonyl)-3-cyclohexyl-1H-indol-1-yl]acetic acid

Product 1

HCID 68507168tert-butyl-2-bromo-1-(2-{(2-bromo-5-chlorobenzyl)[2-(dimethylamino)ethyl]amino}-2-oxoethyl)-3-cyclohexyl-1H-indole-6-carboxylateYield 56%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [2-bromo-6-(tert-butoxycarbonyl)-3-cyclohexyl-1H-indol-1-yl]acetic acid (from Step 7, 1 eq) in DCM (0.07 M), N′-(2-bromo-5-chlorobenzyl)-N,N-dimethylethane-1,2-diamine (from Step 3, 2.1 eq), DIPEA (3 eq) and HATU (2 eq) were added and the mixture stirred at RT overnight. The solution was diluted with DCM and washed with HCl (1 N), a saturated aqueous solution of NaHCO3 and brine, dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (56%) that was used in the next step without further purification; MS (ES+) m/z 710 (M+H)+.

Workup

  1. washwashed with HCl (1 N)
  2. dry with materiala saturated aqueous solution of NaHCO3 and brine, dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-835222a084b24f8e92ff78cb1736c6f4
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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