Isopropylamine → 5-((Isopropylamino)methyl)thiophen-2-ylboronic acid

HRID 562136Notes

Reaction equation

HRID 562136 reaction equation
C(NCC1SC(C2C=[C:12]3[C:16](=[C:17](C(N)=O)C=2)[NH:15]C=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.C(N)(C)C.[BH3-]C#N.[Na+]>>[CH3:12][CH:16]([NH:15][CH2:33][C:35]1[S:39][C:38]([B:40]([OH:42])[OH:41])=[CH:37][CH:36]=1)[CH3:17]

Participants

5

Reactant 4

HCID 6363IsopropylamineHCID 27734305-Formyl-2-thiopheneboronic acidHCID 5003444Sodium cyanoborohydrideHCID 577327795-{5-[(ethylamino)methyl]-2-thienyl}-3-[1-(ethylsulfonyl)-4-piperidinyl]-1H-indole-7-carboxamide

Product 1

HCID 667228665-((Isopropylamino)methyl)thiophen-2-ylboronic acid

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), isopropylamine (0.027 mL, 0.32 mmol), and NaCNBH3 (40 mg, 0.64 mmol) were reacted to give 41 mg of crude (5-{[(1-methylethyl)amino]methyl}-2-thienyl)boronic acid. The crude (5-{[(1-methylethyl)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 74 mg of the title compound (37%).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-111b27a5cc614e85b261777c57bcf4ed
Source dataset
uspto-grants-2011_11
Patent number
US08063071B2

Reaction notes

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