Hydrochloric Acid → HCID 66989054, compound

HRID 888962Notes

Reaction equation

HRID 888962 reaction equation
C([N-]C(C)C)(C)C.[Li+].[C:9]([N:13]1[C:21]2[C:16](=[C:17]([N:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)([CH3:12])([CH3:11])[CH3:10].[B:31](OC(C)C)([O:36]C(C)C)[O:32]C(C)C.Cl>C1COCC1>[C:9]([N:13]1[C:21]2[C:16](=[C:17]([N:22]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:23]([CH3:26])([CH3:25])[CH3:24])[CH:18]=[CH:19][CH:20]=2)[CH:15]=[C:14]1[B:31]([OH:36])[OH:32])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 2724682Lithium diisopropylamideHCID 66988920HCID 66988920, compound

Product 1

HCID 66989054HCID 66989054, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution of lithium diisopropylamide prepared above was added in an ice bath dropwise to a THF (5 mL) solution of 1-(tert-butyl)-4-(di-tert-butyl)aminoindole (300 mg, 0.694 mmol) and triisopropyl borate (157 mg, 0.832 mmol) which was separately prepared. After the reaction solution was stirred in an ice bath for 1 hour, the solution was adjusted to pH3 with adding a 1M HCl solution. The resulting solution was extracted with ethyl acetate (15 mL×2), and the combined solution was dried over anhydrous magnesium sulfate to afford the crude product 53 of 1-(tert-butyl)-4-(ditert-butyl)amino-2-indoleboronic acid. The crude product was used for the next reaction without any further purification.

Workup

  1. customwas separately prepared
  2. extractionThe resulting solution was extracted with ethyl acetate (15 mL×2)
  3. dry with materialthe combined solution was dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-2239fbfb7b5d4f9bb2d96a564111bf13
Source dataset
uspto-grants-2012_08
Patent number
US08252790B2

Reaction notes

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