Triisopropyl borate → HCID 71285344, compound

HRID 1481809Notes

Reaction equation

HRID 1481809 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[C:13]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:12]=[C:11]([C:33]2[CH:34]=[C:35]3[C:39](=[CH:40][CH:41]=2)[N:38]([C:42]([O:44][C:45]([CH3:48])([CH3:47])[CH3:46])=[O:43])[CH:37]=[CH:36]3)[C:10]=1[CH2:49][CH3:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O:54][B:55](OC(C)C)[O:56]C(C)C)(C)C.[Li+].CC([N-]C(C)C)C>C1COCC1>[CH2:1]([O:8][C:9]1[C:14]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])=[C:13]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:12]=[C:11]([C:33]2[CH:34]=[C:35]3[C:39](=[CH:40][CH:41]=2)[N:38]([C:42]([O:44][C:45]([CH3:46])([CH3:48])[CH3:47])=[O:43])[C:37]([B:55]([OH:56])[OH:54])=[CH:36]3)[C:10]=1[CH2:49][CH3:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 21531Triisopropyl borateHCID 2724682Lithium diisopropylamideHCID 71285136HCID 71285136, compound

Product 1

HCID 71285344HCID 71285344, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 5-(4,6-bis(benzyloxy)-5-((benzyloxy)carbonyl)-3-ethylpyridin-2-yl)-1H-indole-1-carboxylate, prepared according to the protocol described in Example 412, step 3 (3.07 g, 4.59 mmol), triisopropylborate (1.17 mL, 5.51 mmol) in THF (15 mL), at −78° C. was added while stirring, LDA (3.67 mL, 1.5 M in cyclohexane, 5.51 mmol). The mixture was stirred for 0.5 h after the addition and the cooling bath was removed to allow the reaction mixture to warm to room temperature and stirred for an additional 0.5 h. The reaction was quenched with 6 N HCl at 0° C. and acidified to pH 4 and the mixture was diluted with DCM and water. The organic layer was separated, washed with water, brine and dried over anhydrous Na2SO4. The filtrate was concentrated and chromatographed (ethyl acetate in DCM, 0-40%) to give the boronic acid intermediate as light yellow powder (0.78 g) in 24% yield.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred for 0.5 h
  3. additionafter the addition
  4. customthe cooling bath was removed
  5. stirringstirred for an additional 0.5 h
  6. customThe reaction was quenched with 6 N HCl at 0° C.
  7. additionthe mixture was diluted with DCM and water
  8. customThe organic layer was separated
  9. washwashed with water, brine
  10. dry with materialdried over anhydrous Na2SO4
  11. concentrationThe filtrate was concentrated
  12. customchromatographed (ethyl acetate in DCM, 0-40%)

Sources & evidence

ORD record
ord-83da68e425ca46b598092ef41977e7ef
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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