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Trimethyl borate → 1H-Indole-1-carboxylic acid, 2-borono-5-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]sulfonyl]-, 1-(1,1-dimethylethyl) ester (9CI)

HRID 2211941
Notes
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Reaction equation

HRID 2211941 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:21]=[CH:20]3)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li]C(C)(C)C.C[O:39][B:40](OC)[O:41]C>C1COCC1>[C:29]([O:28][C:26]([N:22]1[C:23]2[C:19](=[CH:18][C:17]([S:14]([N:11]3[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]3)(=[O:16])=[O:15])=[CH:25][CH:24]=2)[CH:20]=[C:21]1[B:40]([OH:41])[OH:39])=[O:27])([CH3:32])([CH3:31])[CH3:30]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 8470Trimethyl borateHCID 21963096tert-Butyl 5-((4-(tert-butoxycarbonyl)piperazin-1-yl)sulfonyl)-1H-indole-1-carboxylateHCID 178418306HCID 178418306, compound

Product 1

HCID 219630881H-Indole-1-carboxylic acid, 2-borono-5-[[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]sulfonyl]-, 1-(1,1-dimethylethyl) ester (9CI)

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
0 °C

Procedure

A solution of the tert-butyl 5-{[4-(tert-butoxycarbonyl)piperazin-1-yl]sulfonyl}-1H-indole-1-carboxylate (2-4, 1.06 g) in THF (55 mL) was stirred at −78° C. and treated with t-BuLi (1.7M, 2.68 mL, 4.55 mmol). After stirring for 45 minutes, the solution was treated with trimethylborate (640 μL, 5.69 mmol). The solution was warmed to 0° C. and stirred for 10 min, then partitioned between ethyl acetate (2×100 mL) and saturated NH4Cl solution (100 mL). The combined organics were dried over Na2SO4, filtered and concentrated to provide 1-(tert-butoxycarbonyl)-5-{[4-(tert-butoxycarbonyl)piperazin-1-yl]sulfonyl}-1H-indol-2-ylboronic acid (2-5) as a yellow foam. LRMS m/z: Cal'd for C22H32BN3O8S (M+H) 509.39, found 510.1.

Workup

  1. stirringstirred for 10 min
  2. custompartitioned between ethyl acetate (2×100 mL) and saturated NH4Cl solution (100 mL)
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3df5616b985c4c999d3214a2cea20f2d
Source dataset
uspto-grants-2006_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07101884B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes