Triethylamine → HCID 46853448, compound

HRID 1749167Notes

Reaction equation

HRID 1749167 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH:17]([OH:28])[CH2:18][NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.C(N(CC)CC)C>CS(C)=O.C(OCC)(=O)C>[Br:15][C:10]1[CH:9]=[CH:8][C:7]2[N:6]([CH2:16][C:17](=[O:28])[CH2:18][NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=3)[C:5]3[C:13]([C:12]=2[CH:11]=1)=[CH:14][C:2]([Br:1])=[CH:3][CH:4]=3

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 3103961P7C3-OMe

Product 1

HCID 46853448HCID 46853448, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trietheylamine (1.65 ml, 11.8 mmol) was added to a stirring solution of 1-(3,6-dibromo-9H-carbazol-9-yl)-3-(3-methoxyphenylamino)propan-2-ol (1.02 g, 2.02 mmol) in DMSO (21 ml). The solution was stirred for 30 minutes before addition of sulfur trioxide pyridine complex (0.659 g, 4.14 mmol). After stirring overnight, additional triethylamine (1.0 ml, 7.17 mmol) was added, followed by sulfur trioxide pyridine complex (0.663 mg, 4.17 mmol) an hour later. After stirring for 1 h, the orange solution was diluted with ˜150 ml ethyl acetate and washed several times with water and then brine.

Workup

  1. stirringAfter stirring overnight
  2. customfollowed by sulfur trioxide pyridine complex (0.663 mg, 4.17 mmol) an hour
  3. stirringAfter stirring for 1 h
  4. washwashed several times with water

Sources & evidence

ORD record
ord-9fdc3a9112ee4896a2ca4f2715741251
Source dataset
uspto-grants-2015_10
Patent number
US09156787B2

Reaction notes

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