1,2-Dichloroethane → HCID 66606949, compound

HRID 1811145Notes

Reaction equation

HRID 1811145 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-be914db280864c4b937c2fbd51b5b832
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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