Benzene, (2-bromoethoxy)- → HCID 22396828, compound

HRID 2307007Notes

Reaction equation

HRID 2307007 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([Cl:34])[C:7]2[C:8]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22][C:9]=3[N:10]([CH2:13][CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:11]=2[CH:12]=1.[Cl:35]C1C=C(Cl)C2C3CCN(C(OC(C)(C)C)=O)CCC=3NC=2C=1.BrCCOC1C=CC=CC=1>CN(C=O)C>[ClH:3].[Cl:35][C:12]1[C:11]2[N:10]([CH2:13][CH2:14][O:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:9]3[CH2:22][CH2:23][NH:24][CH2:25][CH2:26][C:8]=3[C:7]=2[C:6]([Cl:34])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 68526Benzene, (2-bromoethoxy)-HCID 22396843HCID 22396843, compoundHCID 86590375HCID 86590375, compound

Product 1

HCID 22396828HCID 22396828, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Preparation of tert-Butyl 8,10-dichloro-6-(2-phenoxyethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate Sodium hydride (60% dispersion in mineral oil, 51 mg, 1.3 mmol) was added to a solution of tert-butyl 8,10-dichloro-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.30 g, 0.84 mmol) in DMF (5 mL). After 25 min, β-bromophenetole was added (0.23 mL). The reaction was quenched with saturated aqueous NH4Cl after 18 h and extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude product was purified by column chromatography (Biotage, 40S) with heptane/EtOAc (9:1) to give 0.36 g (90%) of a white solid: mp 131.5-133.0° C.; 1H NMR (300 MHz, CDCl3) δ 7.04 (d, J=1.7 Hz, 1H), 6.94 (t, J=7.4 Hz, 1H), 6.77 (m, 2H), 4.41 (m, 2H), 4.16 (m, 2H), 3.76 (m, 2H), 3.65 (m, 2H), 3.45 (m, 2H), 3.11 (m, 2H), 1.48 (s, 9H); IR (diffuse reflectance) 2974, 2929, 1691, 1600, 1496, 1459, 1413, 1393, 1365, 1348, 1303, 1243, 1170, 1114, 754 cm−1; MS (EI) m/z 474 (M+), 420, 419, 418, 417, 344, 334, 332, 57, 56; Anal. Calcd for C25H28Cl2N2O3: C, 63.16; H, 5.94; N, 5.89; found: C, 63.19; H, 5.99; N, 5.89.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl after 18 h
  2. extractionextracted with EtOAc (3×15 mL)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated
  7. customThe crude product was purified by column chromatography (Biotage, 40S) with heptane/EtOAc (9:1)

Sources & evidence

ORD record
ord-92de1a5f79034059903a83c44d8fe549
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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