1,2-Dichloroethane → HCID 66606949, compound

HRID 661965Notes

Reaction equation

HRID 661965 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][CH:12]([OH:24])[CH2:13][CH2:14][C:15]=1[NH:16]2.[Cl-].[NH4+].C1C=[N:31]C2N(O)N=NC=2C=1.C(Cl)CCl.CCN(C(C)C)C(C)C>CN(C=O)C.C(Cl)Cl>[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]([NH2:31])=[O:22])=[C:17]2[C:9]=1[C:10]1[CH2:11][CH:12]([OH:24])[CH2:13][CH2:14][C:15]=1[NH:16]2

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 66606320HCID 66606320, compound

Product 1

HCID 66606949HCID 66606949, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

Step 2 A solution of 5-(2-fluorophenyl)-3-hydroxy-2,3,4,9-tetrahydro-1H-carbazole-8-carboxylic acid (0.069 g, 0.213 mmol) in DMF (1.07 mL) was treated with ammonium chloride (0.023 g, 0.427 mmol), HOAT (0.058 g, 0.427 mmol), EDC (0.082 g, 0.427 mmol) and DIEA (0.149 mL, 0.853 mmol) and stirred over a weekend. The mixture was diluted with DCM, washed with 5% hydrochloric acid, NaHCO3 (aq), brine and 10% aqueous lithium chloride, dried and concentrated to give 5-(2-fluorophenyl)-3-hydroxy-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a light yellow foam (0.045 g, 65%). Mass spectrum m/z 325.1 (M+H)+.

Workup

  1. washwashed with 5% hydrochloric acid, NaHCO3 (aq), brine and 10% aqueous lithium chloride
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-6303944ce39844d08c6e08058fa4f4db
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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