Ethylene Glycol → HCID 59375126, compound

HRID 1811173Notes

Reaction equation

HRID 1811173 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 (1 H, d, J=8.58 Hz), 7.77 (1 H, d, J=1.10 Hz), 7.75 (1 H, d, J=8.14 Hz), 7.44 (1 H, dd, J=8.36, 1.54 Hz), 7.40 (1 H, d), 3.69 (2 H, t, J=5.17 Hz), 3.32-3.34 (2 H, m), 1.68 (6 H, 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-1ef7af90d2ba406f809701a2935b08bf
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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