Benzo(B)Thiophene-2-Boronic Acid → HCID 59024282, compound

HRID 1678213Notes

Reaction equation

HRID 1678213 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9](I)[CH:10]=1)[NH:7][N:6]=[CH:5]2.B(O)(O)[C:13]1[S:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1.COCCOC.C([O-])([O-])=O.[Na+].[Na+]>O>[S:21]1[C:13]([C:9]2[CH:10]=[C:2]([Br:1])[CH:3]=[C:4]3[C:8]=2[NH:7][N:6]=[CH:5]3)=[CH:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]1=2

Participants

6

Reactant 4

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 590242185-Bromo-7-iodo-1H-indazole

Product 1

HCID 59024282HCID 59024282, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-7-iodo-1H-indazole (Preparation #22a, 30.0 g, 92.9 mmol) and thianapthene-2-boronic acid (21.5 g, 120.7 mmol), DME (480 mL), water (48 mL), Na2CO3 (29.5 g, 279 mmol) and tetrakis triphenylphosphine palladium (0) (8.6 g, 7.43 mmol) was heated at about 90° C. in an oil bath under an atmosphere of nitrogen for about 15 hours. The solvent was removed under reduced pressure and the residue was suspended in a mixture of ethyl acetate (600 mL) and water (300 mL). The mixture was stirred for about 30 minutes and the resulting solid was collected by filtration and dried to yield 7-Benzo[b]thiophen-2-yl-5-bromo-1H-indazole (21.4 g, 70%); (DMSO-d6, 400 MHz) δ 13.63 (s, 1H), 8.24 (s, 1H), 8.05-8.09 (m, 3H), 7.92 (d, 1H), 7.65 (s, 1H), 7.16 (m, 2H); RP-HPLC (Table 1, Method e) Rt=2.69 min; m/z: (M−H)− 328.4.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was suspended in a mixture of ethyl acetate (600 mL) and water (300 mL)
  3. filtrationthe resulting solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-12b75a5ee1d741cbb1ab8f0529636e9b
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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