Ethylene Glycol → HCID 59375126, compound

HRID 661993Notes

Reaction equation

HRID 661993 reaction equation
[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]([OH:18])([CH3:17])[CH3:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:34](O)[CH2:35][OH:36].C([O-])(O)=O.[Na+]>O>[Br:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([C:15]([O:18][CH2:34][CH2:35][OH:36])([CH3:17])[CH3:16])=[CH:11][CH:12]=3)[NH:7][C:6]=2[C:5]([C:19]([NH2:21])=[O:20])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 66605841HCID 66605841, compound2×

Product 1

HCID 59375126HCID 59375126, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-bromo-7-(2-hydroxypropan-2-yl)-9H-carbazole-1-carboxamide (Intermediate 73-2, 300 mg, 0.864 mmol), p-toluenesulfonic acid monohydrate (8.2 mg, 0.043 mmol) and ethylene glycol (1.45 mL) was stirred at rt overnight. The resulting suspension was treated with NaHCO3 (aq) and diluted with water. The precipitate was collected by filtration, washed with water and dried to provide 4-bromo-7-(2-(2-hydroxyethoxy)propan-2-yl)-9H-carbazole-1-carboxamide as a white solid (324 mg, 96%). 1H NMR (400 MHz, methanol-d4) δ 8.65 (1H, d, J=8.58 Hz), 7.77 (1H, d, J=1.10 Hz), 7.75 (1H, d, J=8.14 Hz), 7.44 (1H, dd, J=8.36, 1.54 Hz), 7.40 (1H, d), 3.69 (2H, t, J=5.17 Hz), 3.32-3.34 (2H, m), 1.68 (6H, s). Mass spectrum m/z 413, 415 (M+Na)+.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-a98252a3da9f4a1b9eee2d469ce6a0d8
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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