Neopentylamine → (5-{[(2,2-Dimethylpropyl)amino]methyl}-2-thienyl)boronic acid

HRID 562140Notes

Reaction equation

C(NCC1SC(C2C=C3C(=C(C(N)=O)C=2)NC=C3C2CCN(S(CC)(=O)=O)CC2)=CC=1)C.[CH:33]([C:35]1[S:39][C:38]([B:40]([OH:42])[OH:41])=[CH:37][CH:36]=1)=O.[CH3:43][C:44]([CH3:48])([CH3:47])[CH2:45][NH2:46].[BH3-]C#N.[Na+]>>[CH3:43][C:44]([CH3:48])([CH3:47])[CH2:45][NH:46][CH2:33][C:35]1[S:39][C:38]([B:40]([OH:42])[OH:41])=[CH:37][CH:36]=1

Participants

Reactant 4

HCID 79882Neopentylamine

HCID 27734305-Formyl-2-thiopheneboronic acid

HCID 5003444Sodium cyanoborohydride

HCID 577327795-{5-[(ethylamino)methyl]-2-thienyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Product 1

HCID 66723467(5-{[(2,2-Dimethylpropyl)amino]methyl}-2-thienyl)boronic acidYield 100.4%

Procedure

Following the general procedure of 5-{5-[(ethylamino)methyl]-2-thienyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide, (5-formyl-2-thienyl)boronic acid (50 mg, 0.32 mmol), (2,2-dimethylpropyl)amine (0.037 mL, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 73 mg of crude (5-{[(2,2-dimethylpropyl)amino]methyl}-2-thienyl)boronic acid. The crude (5-{[(2,2-dimethylpropyl)amino]methyl}-2-thienyl)boronic acid was then reacted with 5-bromo-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide (80 mg, 0.193 mmol), potassium carbonate (160 mg, 1.16 mmol), and tetrakis(triphenylphosphine)palladium(0) (5 mg, 0.004 mmol) to give 21 mg of the title compound (21%).

Workup

customwere reacted

Sources & evidence

ORD record: ord-0d8a1856f102467ca561a56a400e2073
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063071B2

Reaction notes

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