Nitrogen → 4-{[(2-Hydroxyethyl)(methyl)amino]methyl}-1-(phenylsulfonyl)-1H-indol-5-ol

HRID 1159813Notes

Reaction equation

HRID 1159813 reaction equation
C(O[C:9]1[CH:17]=[CH:16][C:15]2[N:14]([S:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)(=[O:20])=[O:19])[CH:13]=[CH:12][C:11]=2[C:10]=1[CH:27]=[O:28])C1C=CC=CC=1.[CH3:29][NH:30][CH2:31][CH2:32][OH:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].N#N>ClCCCl>[OH:33][CH2:32][CH2:31][N:30]([CH2:9][C:10]1[C:27]([OH:28])=[CH:17][CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][N:14]2[S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH3:29]

Participants

6

Reactant 4

HCID 947NitrogenHCID 80162-(Methylamino)ethanolHCID 5049666Sodium triacetoxyborohydrideHCID 866182505-(Benzyloxy)-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde2×

Product 1

HCID 595136004-{[(2-Hydroxyethyl)(methyl)amino]methyl}-1-(phenylsulfonyl)-1H-indol-5-ol

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-(Benzyloxy)-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde (50 mg, 0.12 mmol, Intermediate 62) in DCE (3 mL) was added N-methyl ethanolamine, 22 mg (0.26 mmol) and sodium triacetoxyborohydride, 80 mg (0.38 mmol) and the mixture was heated in a sealed test tube at 40° C. over night. The solvent was removed at reduced pressure and the residue was dissolved in MeOH (2 mL), 10% Pd/C, 20 mg was added and the mixture was flushed with N2, NH4+HCOO− (50 mg, 0.8 mmol) was added, the reaction mixture was again flushed with N2 and the reaction mixture was stirred at 40° C. over night. The solvent was removed at reduced pressure, the semisolid was taken up between CHCl3/H2O, washed with H2O (×1), brine (×1), dried (MgSO4) and the solvent was removed at reduced pressure. A sample was withdrawn and purified with on a preparative HPLC, method B, to yield 6.3 mg of a colorless oil. MS (ESI+) for C18H20N2O4S m/z 361 (M+H)+.

Workup

  1. customThe solvent was removed at reduced pressure
  2. dissolutionthe residue was dissolved in MeOH (2 mL)
  3. addition10% Pd/C, 20 mg was added
  4. additionwas added
  5. customthe reaction mixture was again flushed with N2
  6. customThe solvent was removed at reduced pressure
  7. washwashed with H2O (×1), brine (×1)
  8. dry with materialdried (MgSO4)
  9. customthe solvent was removed at reduced pressure
  10. customA sample was withdrawn
  11. custompurified with on a preparative HPLC, method B

Sources & evidence

ORD record
ord-dd483024d7aa42eea5b82f944f78b7b0
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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