1,2-Dichloroethane → HCID 59375058, compound

HRID 1811142Notes

Reaction equation

HRID 1811142 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[C:17]2[C:9]=1[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=1[NH:16]2.C(Cl)CCl.C1C=CC2N(O)N=[N:34]C=2C=1.[OH-].[NH4+]>C1COCC1.C(Cl)Cl.CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:20]=[CH:19][C:18]([C:21]([NH2:34])=[O:22])=[C:17]2[C:9]=1[C:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=1[NH:16]2

Participants

8

Reactant 4

HCID 111,2-Dichloroethane2×HCID 14923Ammonium Hydroxide2×HCID 757711-Hydroxybenzotriazole2×HCID 66606744HCID 66606744, compound

Product 1

HCID 59375058HCID 59375058, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Step 5 A solution of 5-(2-fluorophenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid (0.097 g, 0.314 mmol), EDC (0.072 g, 0.376 mmol) and HOBT (0.058 g, 0.376 mmol) in THF (2.5 mL) and DCM (0.6 mL) was treated with 28% aqueous ammonium hydroxide (0.073 mL, 1.88 mmol). The mixture was stirred overnight. More EDC (0.072 g, 0.376 mmol), HOBT (0.058 g, 0.376 mmol) and 28% aqueous ammonium hydroxide (0.073 mL, 1.88 mmol) were added, and the mixture was heated at 50° C. in a sealed tube for 2 days. The mixture was cooled to rt, dissolved in EtOAc, washed with NaHCO3 (aq) and brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from DCM to 98:2 DCM-methanol) to give 5-(2-fluorophenyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (0.030 g, 30%) as an off-white solid. Mass spectrum m/z 309.0 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to rt
  2. washwashed with NaHCO3 (aq) and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (
  6. washeluting with a gradient from DCM to 98:2 DCM-methanol)

Sources & evidence

ORD record
ord-c1e98c0937ef4cd7bc73d175a12faa18
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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