Lithium Hydroxide → HCID 68485384, compound

HRID 1874954Notes

Reaction equation

HRID 1874954 reaction equation
[Li+].[OH-].[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][CH2:15][O:16][Si](C(C)(C)C)(C)C)[CH:11]=2)[NH:6][C:5]=1[C:24]([O:26]CC)=[O:25]>C1COCC1.CO>[Br:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:13][CH2:14][CH2:15][OH:16])[CH:11]=2)[NH:6][C:5]=1[C:24]([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 68486193HCID 68486193, compound

Product 1

HCID 68485384HCID 68485384, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1 N in water, 4 mL, 4 mmol) was added to a solution of ethyl 3-bromo-5-[(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)oxy]-1H-indole-2-carboxylate (0.121 g, 0.275 mmol) in THF (4 mL) and methanol (4 mL). The solution was stirred at room temp overnight. The reaction mixture was evaporated to a residue and partitioned between EtOAc and 1 N HCl. The organic layer was separated, dried over MgSO4, and evaporated to a crude solid to afford the title compound (0.081 g, 89%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.14-13.33 (m, 1H), 11.97 (s, 1H), 7.34 (d, 1H), 6.97 (dd, 1H), 6.86 (s, 1H), 4.83 (t, 1H), 3.99 (t, 2H), 3.71 (q, 2 H). LC-MS (ES+) m/z 301 [M+H].

Workup

  1. customThe reaction mixture was evaporated to a residue
  2. custompartitioned between EtOAc and 1 N HCl
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. customevaporated to a crude solid

Sources & evidence

ORD record
ord-5f46f39742dd4859ba360608f9922a6c
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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