(4,4-Difluoropiperidin-1-yl)[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]methanone → 4-[2-(4,4-Difluoro-piperidine-1-carbonyl)-1H-indol-5-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

HRID 19893Notes

Reaction equation

HRID 19893 reaction equation
[F:1][C:2]1([F:29])[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([CH:18]=2)=[CH:16][C:15]([O:19][CH:20]2[CH2:25][CH2:24][N:23](C(C)C)[CH2:22][CH2:21]2)=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.Cl.[C:31]([O:35][C:36](N1CCC(OC2C=C3C(=CC=2)NC(C(O)=O)=C3)CC1)=[O:37])([CH3:34])([CH3:33])[CH3:32].C1(N2CCC(OC3C=C4C(=CC=3)N(C3C=NC=NC=3)C(C(N3CCC(F)(F)CC3)=O)=C4)CC2)CCC1>>[C:31]([O:35][C:36]([N:23]1[CH2:24][CH2:25][CH:20]([O:19][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[NH:11][C:10]([C:8]([N:5]2[CH2:6][CH2:7][C:2]([F:29])([F:1])[CH2:3][CH2:4]2)=[O:9])=[CH:18]3)[CH2:21][CH2:22]1)=[O:37])([CH3:34])([CH3:33])[CH3:32]

Participants

4

Reactant 3

HCID 11603838(4,4-Difluoropiperidin-1-yl)[5-(1-isopropyl-piperidin-4-yloxy)-1H-indol-2-yl]methanoneHCID 16739661[5-(1-Cyclobutyl-piperidin-4-yloxy)-1-pyrimidin-5-yl-1H-indol-2-yl]-(4,4-difluoro-piperidin-1-yl)-methanoneHCID 670179225-(1-Tert-butoxycarbonyl-piperidin-4-yloxy)-1h-indole-2-carboxylic acid hydrochloride salt

Product 1

HCID 670179124-[2-(4,4-Difluoro-piperidine-1-carbonyl)-1H-indol-5-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

Procedure

In analogy to the procedure described for the synthesis of intermediate 1, step 4, the title compound was synthesized from 5-(1-tert-butoxycarbonyl-piperidin-4-yloxy)-1H-indole-2-carboxylic acid hydrochloride salt with 1 eq. lithium chloride (example 43, step 4). The title compound was obtained in 59% yield as white solid. MS (m/e): 464.3 (MH+, 75%).

Sources & evidence

ORD record
ord-ddc4b27a543441a58dca287c82b3147e
Source dataset
uspto-grants-2010_06
Patent number
US07745479B2

Reaction notes

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