Chloroform → HCID 67598117, compound

HRID 1490272Notes

Reaction equation

HRID 1490272 reaction equation
[CH:1]1[C:17]2[CH:16]=[C:15]3[C:7](=[C:8]4[C:13](=[N:14]3)[CH:12]=[CH:11][CH:10]=[CH:9]4)[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+].C(Cl)(Cl)[Cl:33]>>[Cl-:33].[CH2:18]([N+:6]1[C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:14]([CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:15]=2[CH:16]=[C:17]2[C:5]=1[CH:4]=[CH:3][CH:2]=[CH:1]2)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 4

HCID 6212ChloroformHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 178420006HCID 178420006, compound

Product 1

HCID 67598117HCID 67598117, compoundYield 32.7%

Conditions

Temperature
140 °C

Procedure

A suspension of quindoline (1 g, 4.58 mmol) from Example 2, benzyl bromide (3 mL, 25.1 mmol) and dry chloroform (5 mL) was heated in a bomb at 140° C. for 48 hours. A solution of aqueous 5% Na2CO3 (100 mL) was added and the reaction mixture was extracted with chloroform (2×250 mL). The extract was evaporated to dryness. The residue was purified on a basic alumina column eluting with 1-2% MeOH in CHCl3, and the combined fractions were acidified with a solution of 1.0M HCl in ether and concentrated to afford 0.65 g (32.7%) of the title compound as an orange solid, mp 244.4°-244.7° C.; 1H NMR (DMSO-d6) δ 9.87 (s, 1H), 8.59 (d, J=8.0, 1H), 8.55 (d, J=9.2, 1H), 8.37 (d, J=8.4, 1H), 8.04-7.93 (m, 3H), 7.45 (t, J=7.2, 1H), 7.40-7.28 (m, 10 H), 6.87 (s, 2H), 6.06 (s, 2H); 13C NMR (DMSO-d6) δ 145.84, 138.05, 136.03, 135.36, 134.74, 134.46, 133.29, 133.14, 130.13, 129.19, 128.81, 128.18, 127.84, 127.65, 126.95, 126.49, 126.08, 125.63, 125.13, 122.13, 117.78, 113.11, 111.99, 55.17, 46.28; MS (LSIMS, m/z) 399 (MH+).

Workup

  1. extractionthe reaction mixture was extracted with chloroform (2×250 mL)
  2. customThe extract was evaporated to dryness
  3. customThe residue was purified on a basic alumina column
  4. washeluting with 1-2% MeOH in CHCl3
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-023e787bb8864d0d85b1fdf6f391be12
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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