Hydrochloric Acid → 5-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester

HRID 1633643Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:18]([OH:23])[CH2:19][CH2:20][C:21]#[CH:22].Cl>N1CCCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:22]#[C:21][CH2:20][CH2:19][CH2:18][OH:23])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

To 3.73 g (12.5 mmol) 5-Bromo-indole-1-carboxylic acid tert-butyl ester in 25 ml piperidine were added 722 mg (0.63 mmol) tetrakis-(triphenylphosphine)-palladium and 120 mg (0.625 mmol) CuI. The solution was purged with argon, and was heated to 80° C. over a period of 45 min, during which 0.9 ml (9.4 mmol) 4-pentynol were added. Additional 0.9 ml (9.4 mmol) 4-pentynol were added and the mixture was stirred at 80° C. for 2 h, poured on ice water and 2M HCl was added. The inorganic phase was extracted with ether, the organic phases were washed with water and dried over Na2SO4. Purification on silica gel yielded 2.9 g (77%) 5-(5-Hydroxy-pent-1-ynyl)-indole-1-carboxylic acid tert-butyl ester as brown oil, MS: 299 (M).

Workup

customThe solution was purged with argon
additionwere added
additionwas added
extractionThe inorganic phase was extracted with ether
washthe organic phases were washed with water
dry with materialdried over Na2SO4
customPurification on silica gel

Sources & evidence

ORD record: ord-fe8ab128d93c4547a4b7a4fcb46dc7c4
Source dataset: uspto-grants-2003_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06503907B2

Reaction notes

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