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Sodium Carbonate → HCID 178504259, compound

HRID 1615369
Notes
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Reaction equation

HRID 1615369 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=1.[NH:21]1[C:25]([C:26]2[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=2)=[N:24][N:23]=[N:22]1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.CCO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH:24]1[C:25]([C:26]2[CH:31]=[C:30]([C:2]3[C:10]4[C:5](=[CH:6][C:7]([CH:11]=[O:12])=[CH:8][CH:9]=4)[N:4]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:3]=3)[CH:29]=[CH:28][CH:27]=2)=[N:21][N:22]=[N:23]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 581896963-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehydeHCID 178514832HCID 178514832, compound

Product 1

HCID 178504259HCID 178504259, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 86587095Dimethoxyethane ethanol waterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (100 mg, 0.25 mmol), 3-(tetrazol-5-yl)phenylboronic acid (57 mg, 0.30 mmol), Pd(PPh3)4 (18 mg, 0.025 mmol) and 2M Na2CO3 (0.13 mL, 0.25 mmol) in DME/H2O/EtOH (2.8 mL/0.8 mL/0.4 mL) was degassed by evacuation and blanketed with Ar. The reaction mixture was sealed and heated with stirring under microwave irradiation at 125° C. for 4 hours. The crude reaction mixture was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel using MeOH (5% to 10%) in DCM as the eluent to provide a white solid (40 mg, 38%). 1H NMR (400 MHz, CD3OD) δ ppm 10.10 (s, 1H), 8.59 (s, 1H), 8.25 (s, 1H), 8.21 (d, J=8.5 Hz, 1H), 8.11 (d, J=7.9 Hz, 1H), 8.04 (d, J=8.3 Hz, 1H), 7.77 (d, J=8.4 Hz, 1H), 7.67 (t, J=7.8 Hz, 1H), 5.88 (s, 2H), 3.66 (t, J=8.1 Hz, 2H), 0.89 (t, J=8.0 Hz, 2H), −0.10 (s, 9H); MS ESI 421.1 (100) [M+H]+, calcd for [C21H24N6O2Si+H]+ 421.2.

Workup

  1. customwas degassed by evacuation
  2. customThe reaction mixture was sealed
  3. temperatureheated
  4. customThe crude reaction mixture
  5. concentrationwas concentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b026c6958e9c4e1ea4a9371fdb979887
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765748B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes