Dimethylformamide → 9-(2-Fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride

HRID 628720Notes

Reaction equation

HRID 628720 reaction equation
[F:1][CH2:2][CH2:3][N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH:12]([C:17]([OH:19])=O)[C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.C(Cl)(=O)C([Cl:23])=O.CN(C=O)C>ClCCl>[F:1][CH2:2][CH2:3][N:4]1[C:16]2[CH2:15][CH2:14][CH2:13][CH:12]([C:17]([Cl:23])=[O:19])[C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 666800789-(2-fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid

Product 1

HCID 866614249-(2-Fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chlorideYield 102%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9-(2-Fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carboxylic acid (31) (0.5 g, 1.91 mmol) in dry dichloromethane (6 mL) was stirred under an atmosphere of nitrogen at room temperature with oxalyl chloride (490 mg, 3.8 mmol, 0.34 mL) and a drop of DMF. The reaction was concentrated in vacuo to afford 545 mg (quantitative) of 9-(2-fluoro-ethyl)-2,3,4,9-tetrahydro-1H-carbazole-4-carbonyl chloride (32) which was used in the next step without purification. The structure was confirmed by 13C NMR (75 MHz, CDCl3) δC 20.2, 21.6, 26.7, 43.1, 43.4, 50.6, 80.9, 83.1, 105.3, 108.8, 118.3, 120.0, 121.6, 126.5, 136.2, 137.5, 176.1.

Workup

  1. concentrationThe reaction was concentrated in vacuo

Sources & evidence

ORD record
ord-f36c3e02929245bf82ec647a9db8e6bf
Source dataset
uspto-grants-2016_04
Patent number
US09314541B2

Reaction notes

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