Propionyl chloride → HCID 18367820, compound

HRID 379908Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[C:17]([C:19]1[C:24]([CH2:25][O:26][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])=[CH:23][CH:22]=[CH:21][N:20]=1)=[O:18].[C:34](Cl)(=[O:37])[CH2:35][CH3:36]>>[Si:27]([O:26][CH2:25][C:24]1[C:19]([C:17]([C:3]2[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]3[C:10]([C:2]=2[NH:1][C:34](=[O:37])[CH2:35][CH3:36])=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=3)=[O:18])=[N:20][CH:21]=[CH:22][CH:23]=1)([C:30]([CH3:32])([CH3:31])[CH3:33])([CH3:29])[CH3:28]

Participants

Reactant 2

HCID 62324Propionyl chloride

HCID 18367778HCID 18367778, compound

Product 1

HCID 18367820HCID 18367820, compound

Procedure

The title compound was prepared according to the procedure described in step 1 of Example 2 employing 3-amino-2-[3-(tert-butyldimethylsilyloxymethyl)pyridine-2-carbonyl]-6-chloro-1-(ethoxycarbonyl)indole (step 3) and propionyl chloride. 1H-NMR (CDCl3) δ: 9.48 (1 H, br s), 8.45 (1 H, dd, J=1.5, 4.5 Hz), 8.25 (1 H, dd, J=1.5, 8.1 Hz), 8.16 (1 H, d, J=1.8 Hz), 8.08 (1 H, d, J=8.9 Hz), 7.44 (1 H, dd, J=4.6, 7.9 Hz), 7.25 (1 H, dd, J=1.8, 8.8 Hz), 5.20 (2 H, s), 3.86 (2 H, q, J=7.1 Hz), 2.50 (2 H, q, J=7.6 Hz), 1.26 (3 H, t, J=7.6 Hz), 1.00 (9 H, s), 1.00 (3 H, t, J=7.0 Hz), 0.18 (6 H, s).

Sources & evidence

ORD record: ord-fbd60da019b34a58bc415e39d07f1b27
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300363B1

Reaction notes

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