Triethylamine → HCID 86686449, compound

HRID 2176812Notes

Reaction equation

HRID 2176812 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].C(N(CC)CC)C>ClCCl>[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, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(pentan-2-yl)-1H-indol-5-ol (9) (2.60 g, 12.8 mmol) in dichloromethane (CH2Cl2, 40 mL) was added isopropyl isocyanate (10) (i-PrNCO, 1.63 g, 19.3 mmol), followed by triethylamine (NEt3, 0.90 mL). The solution was stirred at room temperature overnight, and then concentrated to dryness in vacuo. The resulting oil was purified by silica gel column chromatography (1:3 ethyl acetate/hexanes) to provide 1-(pentan-2-yl)-1H-indol-5-yl isopropylcarbamate (11) (3.6 g, 98%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.35 (d, J=2.0, 1H), 7.32 (d, J=9.0 Hz, 1H), 7.22 (d, J=3.0 Hz, 1H), 6.98 (dd, J=8.5, 2.0, 1H), 6.50 (d, J=3.0 Hz, 1H), 4.86 (d, J=6.5 Hz, 1H), 4.49 (m, 1H), 3.82 (m, 1H), 1.87 (m, 2H), 1.51 (d, J=6.5, 3H), 1.26 (m, 8H), 0.90 (t, J=7.5, 3H).

Workup

  1. concentrationconcentrated to dryness in vacuo
  2. customThe resulting oil was purified by silica gel column chromatography (1:3 ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-02ea58a5678a413fb62091abb9d8458d
Source dataset
uspto-grants-2015_06
Patent number
US09067886B2

Reaction notes

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