Triethylamine → HCID 86686449, compound

HRID 2176817Notes

Reaction equation

HRID 2176817 reaction equation
[CH3:1][CH:2]([N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)[CH2:3][CH2:4][CH3:5].[CH:16]([N:19]=[C:20]=[O:21])([CH3:18])[CH3:17].CCN(CC)CC>C(Cl)Cl>[CH:16]([NH:19][C:20](=[O:21])[O:15][C:11]1[CH:10]=[C:9]2[C:14](=[CH:13][CH:12]=1)[N:6]([CH:2]([CH2:3][CH2:4][CH3:5])[CH3:1])[CH:7]=[CH:8]2)([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 86686448HCID 86686448, compound

Product 1

HCID 86686449HCID 86686449, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(pentan-2-yl)-1H-indol-5-ol (9) in CH2Cl2 (180 mL) was added i-PrNCO (5.37 mL, 54.6 mmol, 1.5 equiv.) and NEt3 (1.52 mL, 10.9 mmol, 0.30 equiv.), respectively. The reaction mixture was stirred at room temperature for 21 h, then concentrated to dryness in vacuo affording a dark, viscous liquid. The crude product was purified by flash column chromatography (2:1 hexanes/ethyl acetate) to give a beige solid, which was further purified by recrystallization from 100 mL of hexanes. Analytically pure product (11) was obtained as a white solid (6.29 g, 55% three-step yield). 1H NMR (500 MHz, CDCl3) δ7.33 (d, J=2.1 Hz, 1H), 7.31 (d, J=8.9 Hz, 1H), 7.19 (dd, J=8.8, 2.2 Hz, 1H), 6.47 (d, J=3.1 Hz, 1H), 4.83 (d, J=6.6 Hz, 1H), 4.45 (m, 1H), 3.91 (m, 1H), 1.87 (m, 1H), 1.76 (m, 1H), 1.48 (d, J=6.8 Hz, 3H), 1.30-1.13 (m, 8H), 0.87 (t, J=7.4 Hz, 3H).

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. customaffording a dark, viscous liquid
  3. customThe crude product was purified by flash column chromatography (2:1 hexanes/ethyl acetate)
  4. customto give a beige solid, which
  5. customwas further purified by recrystallization from 100 mL of hexanes

Sources & evidence

ORD record
ord-4a164a771d444765a219455feadb19c5
Source dataset
uspto-grants-2015_06
Patent number
US09067886B2

Reaction notes

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