5-Aminoindole → 4-[7-Benzenesulfonyl-4-(1H-indol-5-ylamino)-7H-pyrrolo[2,3-d]-pyrimidin-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester

HRID 2375820Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:23]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:17]3[N:18]=[CH:19][N:20]=[C:21](Cl)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:33][C:34]1[CH:35]=[C:36]2[C:40](=[CH:41][CH:42]=1)[NH:39][CH:38]=[CH:37]2>C(O)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[N:23]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[C:17]3[N:18]=[CH:19][N:20]=[C:21]([NH:33][C:34]4[CH:35]=[C:36]5[C:40](=[CH:41][CH:42]=4)[NH:39][CH:38]=[CH:37]5)[C:16]=3[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

4-(7-Benzenesulfonyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (150 mg, 0.31 mmol) in butanol (5 mL) was treated with 5-aminoindole (50 mg, 0.38 mmol) and heated to 80° C. for 2 h and then 85° C. for 1 h. The mixture was evaporated to dryness and pre-absorbed onto silica. Purification on silica by elution with dichloromethane:methanol (97:3) yielded a slightly pink solid. 1H NMR (d6-DMSO, 400 MHz) 9.4(NH), 8.3(1H, s), 8.0(2H,d), 7.9(1H,s), 7.7(1H,m), 7.6(2H,m), 7.4(2H,m), 7.2(1H,m), 6.8(1H, br.s), 6.4(1H, s), 6.0(1H,s), 4.1(2H, m), 3.6(2H,m), 2.5(2H, m), and 1.5(9H, s); LC/MS: m/z 570 [M+H]+, Rt=4.07 min.

Workup

customThe mixture was evaporated to dryness
custompre-absorbed onto silica
customPurification on silica
washby elution with dichloromethane:methanol (97:3)
customyielded a slightly pink solid

Sources & evidence

ORD record: ord-86cd6ea4b3e941329fe84e5021d7c837
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07465726B2

Reaction notes

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