Aluminum(III) Chloride → HCID 22676771, compound

HRID 1006280Notes

Reaction equation

HRID 1006280 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]([O:7][C:8]([C:10]1[N:11]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[CH:36]=2)[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:29]([CH:31]1[CH2:33][CH2:32]1)=O)=[O:9])[CH3:6]>ClCCl>[CH2:5]([O:7][C:8]([C:10]1[N:11]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([O:41][CH3:42])[CH:36]=2)[C:12]2[C:17]([C:18]=1[C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:26])[CH3:27])=[CH:21][CH:20]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[CH2:29][CH:31]1[CH2:32][CH2:33]1)=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 22676720HCID 22676720, compound

Product 1

HCID 22676771HCID 22676771, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Aluminum chloride (0.24 g, 2 eq.) was suspended in dichloromethane (20 mL) and cooled to 0° C. Borane-t-butylamine complex (0.14 g, 1.8 eq.) was added slowly, and the mixture was stirred for 30 minutes. A solution of ethyl-3-(4-t-butylphenyl)-7-(cyclopropyl)carbonyl-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 201, 0.405 g, 0.9 mmol.) in dichloromethane (5 mL) was added, and the reaction was stirred for two hours. The mixture was quenched with water and diluted with dichloromethane. The organic layer was washed with 1N HCl and saturated sodium bicarbonate, dried over sodium sulfate, then purified by flash chromatography over silica to give 0.26 g (62%.) The desired product had: 1H NMR (300 MHz, CDCl3) 7.21-7.4 (m, 5 H), 7.11 (d, 1 H), 7.02 (t, 1 H), 6.95 (t, 1 H), 6.59 (d, 1H), 6.35 (m, 2 H), 5.9 (s, 2 H), 3.9 (q, 2 H), 3.58 (s, 3 H), 2.75 (d, 2 H), 1.26 (s, 9 H), 0.85 (t, 3 H), 0.4 (m, 2 H), 0.02 (m, 2H).

Workup

  1. additionBorane-t-butylamine complex (0.14 g, 1.8 eq.) was added slowly
  2. stirringthe reaction was stirred for two hours
  3. customThe mixture was quenched with water
  4. additiondiluted with dichloromethane
  5. washThe organic layer was washed with 1N HCl and saturated sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. custompurified by flash chromatography over silica

Sources & evidence

ORD record
ord-b6c04b34fdcc43f2992abf58105ea9b8
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

Loading…