3-Amino-6-bromopicolinic acid → cis (+/-)-Tert-butyl 1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-5-(hydroxymethyl)piperidin-3-ylcarbamate

Participants

Role	Name	HCID	Charge
Reactant	3-Amino-6-bromopicolinic acid	HCID 45480452	—
Reactant	cis (+/-)-Tert-butyl 1-(3-aminopyridin-4-yl)-5-((tert-butyldimethylsilyloxy)methyl)piperidin-3-ylcarbamate	HCID 131731822	—
Product	cis (+/-)-Tert-butyl 1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-5-(hydroxymethyl)piperidin-3-ylcarbamate	HCID 131731821	—

Reaction Steps

Following Method 11 of Example 305, cis (+/−)-tert-butyl 1-(3-aminopyridin-4-yl)-5-((tert-butyldimethylsilyloxy)methyl)piperidin-3-ylcarbamate and 6-bromo-3-aminopicolinic acid were coupled. Following purification by RP HPLC the product fractions were allowed to stand at it overnight in the 0.1% TFA acetonitrile/water solution which removed the silyl group. Upon subsequent lyophilization, cis (+/−)-tert-butyl 1-(3-(3-amino-6-bromopicolinamido)pyridin-4-yl)-5-(hydroxymethyl)piperidin-3-ylcarbamate was obtained and used in Suzuki reactions directly. LCMS (m/z): 521.0/523.1 (MH+); LC Rt=2.58 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08822497B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-1f087e42ddaf47c0b9fd6a5ef75c26dc
Source note	uspto-grants-2014_09