Formic Acid → HCID 71251281, compound

Participants

Role	Name	HCID	Charge
Reactant	Formic Acid	HCID 284	—
Reactant	5-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 57597747	—
Reactant	5-fluoro-1-((4-methylphenyl)sulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine	HCID 67285690	—
Reactant	HCID 71247905	HCID 71247905	—
Solvent	Acetonitrile	HCID 6342	—
Product	HCID 71251281	HCID 71251281	—

Reaction Steps

Compound 94 was synthesized in a manner similar to 3-(1-Adamantyl)-3-[[5-fluoro-2-(5-fluoro-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidin-4-yl]amino]propionic acid, 86, using 5-chloro-1-(p-tolylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine instead of boronate ester, 7a: 1H NMR (400 MHz, CD3OD) δ 9.02 (d, J=2.3 Hz, 1H), 8.40-8.24 (m, 2H), 8.18 (d, J=5.0 Hz, 1H), 4.91 (d, J=11.6 Hz, 1H), 2.88 (dd, J=16.0, 2.8 Hz, 1H), 2.65 (dd, J=15.9, 11.0 Hz, 1H), 2.01 (s, 3H), 1.77 (dd, J=27.9, 11.9 Hz, 12H); LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=2.60 minutes (M+H) 470.27.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09394302B2
Source dataset	uspto-grants-2016_07
ORD ID	ord-718108ec9c2c46ffa7bf7baff7a6d494
Source note	uspto-grants-2016_07