Water → HCID 68691513, compound

HRID 2238413Notes

Reaction equation

HRID 2238413 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]3[N:12](C(=O)C(F)(F)F)[CH2:11][CH:10]([CH2:25][Cl:26])[C:9]=3[C:8]=2[CH:27]=1)(=[O:3])[CH3:2].C([O-])([O-])=O.[Cs+].[Cs+].O>CO.C(Cl)Cl>[ClH:26].[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]3[NH:12][CH2:11][CH:10]([CH2:25][Cl:26])[C:9]=3[C:8]=2[CH:27]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 10796Cesium carbonateHCID 44549153HCID 44549153, compound

Product 1

HCID 68691513HCID 68691513, compoundYield 202.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 175 (45 mg, 0.11 mmol) and Cs2CO3 (38 mg, 0.11 mmol) in MeOH (3 mL) and CH2Cl2 (6 mL) was stirred for 15 min. Water w added and the mixture was extracted with EtOAc (×3). The combined EtOAc extras were washed with water (×2), brine (×3), dried, and evaporated. The residue was dissolved in HCl(g) saturated dioxane (5 mL) and stirred for 1 h. The dioxane was evaporated to give 8-acetyl-1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole hydrochloride (176) (38 mg, 100%): mp>300° C.; 1H NMR [(CID3)2SO] (two H not observed) 8.42 (d, J=1.3 Hz, 1 H), 8.19 (d, J=9.1 Hz, 1H), 7.80 (dd, J=9.1, 1.7 Hz, 1H), 7.77 (s, 1H), 4.41-4.33 (m, 1H), 3.96 (dd, J=11.0, 4.1 Hz, 1H), 3.85 (t, J=10.1 Hz, 1H), 3.77 (dd, J=11.0, 2.6 Hz, 1H), 3.73 (dd, J=10.3, 2.7 Hz, 1H), 2.74 (s, 3H); 13C NMR δ 197.9, 150.0, 147.1, 135.3, 130.0, 127.1, 124.3, 123.6, 121.6, 119.8, 111.0, 50.8, 46.6, 42.7, 26.8. This material was used directly in the next step.

Workup

  1. extractionthe mixture was extracted with EtOAc (×3)
  2. washThe combined EtOAc extras were washed with water (×2), brine (×3)
  3. customdried
  4. customevaporated
  5. dissolutionThe residue was dissolved in HCl(g) saturated dioxane (5 mL)
  6. customThe dioxane was evaporated

Sources & evidence

ORD record
ord-c8bebb4c2f8344669398e4f1f3e03649
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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